rac-2-Hydroxy-2,8-dimethyl-4-morpho­linoethyl-1-thia-4-aza­spiro­[4.5]decan-3-one

Akkurt, M.; Yalçın, Ş.P.; Klip, N.T.; Büyükgüngör, O.

doi:10.1107/S1600536808022447

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1574-o1575

doi:10.1107/S1600536808022447

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rac-2-Hydroxy-2,8-dimethyl-4-morpholinoethyl-1-thia-4-azaspiro[4.5]decan-3-one

Mehmet Akkurt,^a ^* Şerife Pınar Yalçın,^a Nalan Terzioğlu Klip ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, İIstanbul University, Beyazıt 34116, Istanbul, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 16 July 2008; accepted 17 July 2008; online 23 July 2008)

The title compound, C₁₆H₂₈N₂O₃S, is dimerized by inversion symmetry-related intermolecular O—H⋯N hydrogen bonding, forming an R₂²(16) motif. The dimers are also linked through intermolecular C—H⋯O hydrogen bonding. The compound is chiral with a stereogenic centre located in the thiazole ring, but in the crystal structure it forms a racemate. The thiazole ring has an envelope conformation, while the cyclohexane and morpholine rings adopt chair conformations.

Related literature

For general background, see: Andres et al. (2000 ); Çapan et al. (1999 ); Srivastava et al. (2005 ). For related literature and bond-length data, see: Akkurt et al. (2007 ); Akkurt, Yalçın, Güzeldemirci et al. (2008 ); Akkurt, Yalçın, Klip et al. (2008 ). For ring conformation puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₂₈N₂O₃S
M_r = 328.47
Triclinic, $[P \overline 1]$
a = 8.0753 (4) Å
b = 10.2002 (5) Å
c = 11.8734 (6) Å
α = 82.467 (4)°
β = 71.487 (4)°
γ = 68.965 (4)°
V = 865.44 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.73 × 0.45 × 0.29 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.867, T_max = 0.944
18220 measured reflections
3693 independent reflections
3319 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.093
S = 1.04
3693 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2ⁱ	0.82	2.00	2.8104 (14)	169
C7—H7B⋯S1	0.97	2.82	3.2235 (18)	106
C14—H14B⋯O1ⁱⁱ	0.97	2.52	3.221 (2)	129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022447/kp2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022447/kp2184Isup2.hkl

checkCIF report

Comment top

Thiazolidinones and their spiroheterocyclic analogues have been reported to exhibit antibacterial (Andres et al., 2000), antifungal (Çapan et al., 1999) and antimycobacterial (Srivastava et al., 2005) activity. In view of these observations, we synthesized the title spiro[4.5]decane derivative as a racemate and report its crystal structure.

In the title molecule (Fig. 1), the values of the geometric parameters are normal and comparable with those in the similar compound, 8-methyl-4-morpholinoethyl-1-thia- 4-azaspiro[4.5]decan-3-one (Akkurt, Yalçın, Klip et al., 2008), which is a spiro[4.5]decane derivative.

The title compound is dimerized by inversion-symmetry related intermolecular O—H···N hydrogen bonds, forming an R₂²(16) motif (Bernstein et al.,1995) (Fig. 2). The dimers are interlinked through intermolecular C—H···O hydrogen bonds. The compound is chiral with a stereogenic centre C1, in the thiazole ring. As the structure is centrosymmetric, racemate occurs in the crystal. The thiazole ring (C1–C3/S1/N1) has an envelope conformation on S1 [puckering parameters (Cremer & Pople, 1975): Q(2) = 0.1885 (12) Å, ϕ(2) = 5.7 (4) °]. The cyclohexane and morpholine rings (C3–C8) and (C12–C15/N2/O2) adopt chair conformations [puckering parameters: Q_T = 0.563 (2) Å, θ = 177.6 (2) °, ϕ = 58 (4) °, and Q_T = 0.576 (2) Å, θ = 0.28 (15) °, ϕ = 340 (60) °, respectively].

The structure is stabilized by intramolecular C—H···S and intermolecular O—H···N and C—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature top

For general background, see: Andres et al. (2000); Çapan et al. (1999); Srivastava et al. (2005). For related literature and bond-length data, see: Akkurt et al. (2007); Akkurt, Yalçın, Güzeldemirci et al. (2008); Akkurt, Yalçın, Klip et al. (2008). For ring conformation puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of morpholinoethylamin (5 mmol), 4-methyl cyclohexanone (5 mmol) and α-mercaptopropionic acid (20 mmol) in dry benzene (20 ml) was refluxed for 18 h using a Dean-Stark water separator. Excess solvent was evaporated in vacuo. The residue was taken up in chloroform. The chloroform layer was triturated with saturated NaHCO₃ solution (2x) before drying over sodium sulfate and concentrated under reduced pressure to dryness. The crude product was triturated with diethyl ether several times and recrystallized from ethanol to yield racemic mixture as colourless prisms. IR (ν, cm^-1): 1678 (C=O). ¹H-NMR (δ, DMSO-d₆, 400 MHz): 0.84 (3H, d, J=6.0 Hz, 8-CH₃), 0.96–1.03 (1H, m, cycl. CH), 1.15–1.24 (1H, m, cycl.CH), 1.32–1.42 (3H, m, cycl.CH), 1.51–1.52 (1H, m, cycl.CH), 1.66 (2H, d, J=12.8 Hz, cycl.CH), 1.79 (1H, dd, J=12.8, 2.8 Hz, cycl.CH), 1.95- 2.10 (3H, m, SCHCH₃), 2.33–2.44 (6H, m, morph.N—CH₂), 3.30–3.37 (3H, m, SCH and N—CH₂), 3.54 (4H, t, J=4.4 Hz, OCH₂). LC—MS (m/z): 313 (M+1).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The ORTEP diagram of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the dimer generated by inversion symmetry related O—H···N hydrogen bonds, forming a R₂²(16) motif. For clarity, H atoms not involved in hydrogen bonds have been omitted.

rac-2-Hydroxy-2,8-dimethyl-4-morpholinoethyl-1-thia-4- azaspiro[4.5]decan-3-one top

Crystal data top

C₁₆H₂₈N₂O₃S	Z = 2
M_r = 328.47	F(000) = 356
Triclinic, P1	D_x = 1.260 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0753 (4) Å	Cell parameters from 29023 reflections
b = 10.2002 (5) Å	θ = 2.1–27.4°
c = 11.8734 (6) Å	µ = 0.20 mm⁻¹
α = 82.467 (4)°	T = 296 K
β = 71.487 (4)°	Block, colourless
γ = 68.965 (4)°	0.73 × 0.45 × 0.29 mm
V = 865.44 (8) Å³

Data collection top

Stoe IPDS-2 diffractometer	3693 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3319 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.038
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.9°, θ_min = 2.1°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.867, T_max = 0.944	l = −15→15
18220 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0478P)² + 0.1524P] where P = (F_o² + 2F_c²)/3
3693 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₂₈N₂O₃S	γ = 68.965 (4)°
M_r = 328.47	V = 865.44 (8) Å³
Triclinic, P1	Z = 2
a = 8.0753 (4) Å	Mo Kα radiation
b = 10.2002 (5) Å	µ = 0.20 mm⁻¹
c = 11.8734 (6) Å	T = 296 K
α = 82.467 (4)°	0.73 × 0.45 × 0.29 mm
β = 71.487 (4)°

Data collection top

Stoe IPDS-2 diffractometer	3693 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3319 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.944	R_int = 0.038
18220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.04	Δρ_max = 0.31 e Å⁻³
3693 reflections	Δρ_min = −0.21 e Å⁻³
199 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.33771 (4)	0.24227 (4)	0.79561 (3)	0.0486 (1)
O1	0.45350 (15)	0.25388 (12)	0.45525 (9)	0.0555 (3)
O2	1.23062 (15)	0.29531 (12)	0.15285 (9)	0.0597 (3)
O3	0.11938 (12)	0.32395 (10)	0.65362 (9)	0.0480 (3)
N1	0.59680 (14)	0.23670 (11)	0.59509 (9)	0.0389 (3)
N2	0.90885 (14)	0.39307 (11)	0.34820 (9)	0.0372 (3)
C1	0.28811 (17)	0.22315 (13)	0.65981 (12)	0.0417 (4)
C2	0.45358 (17)	0.24085 (13)	0.55883 (11)	0.0408 (3)
C3	0.58346 (16)	0.22120 (13)	0.72210 (10)	0.0369 (3)
C4	0.7085 (2)	0.07643 (14)	0.75151 (12)	0.0482 (4)
C5	0.7034 (2)	0.06187 (17)	0.88162 (14)	0.0583 (5)
C6	0.7495 (2)	0.17691 (19)	0.92078 (13)	0.0587 (5)
C7	0.6200 (2)	0.31982 (17)	0.89350 (13)	0.0541 (5)
C8	0.62959 (19)	0.33651 (14)	0.76215 (12)	0.0445 (4)
C9	0.7389 (3)	0.1587 (3)	1.05180 (17)	0.0881 (8)
C10	0.76951 (17)	0.23709 (13)	0.50474 (11)	0.0413 (3)
C11	0.75792 (17)	0.38482 (13)	0.45390 (11)	0.0408 (3)
C12	0.90146 (19)	0.34106 (16)	0.24137 (11)	0.0471 (4)
C13	1.0540 (2)	0.36400 (19)	0.13593 (12)	0.0584 (5)
C14	1.2384 (2)	0.34737 (18)	0.25562 (13)	0.0554 (5)
C15	1.09318 (17)	0.32359 (15)	0.36461 (11)	0.0432 (4)
C16	0.2750 (2)	0.08031 (15)	0.65024 (15)	0.0561 (5)
H3	0.12210	0.40260	0.65820	0.0720*
H4A	0.66870	0.00470	0.73310	0.0580*
H4B	0.83500	0.06140	0.70220	0.0580*
H5A	0.58070	0.06390	0.93020	0.0700*
H5B	0.79130	−0.02850	0.89480	0.0700*
H6	0.87690	0.16960	0.87490	0.0700*
H7A	0.65370	0.39320	0.91510	0.0650*
H7B	0.49370	0.33050	0.94100	0.0650*
H8A	0.54300	0.42730	0.74850	0.0530*
H8B	0.75330	0.33370	0.71510	0.0530*
H9A	0.82270	0.06800	1.06540	0.1320*
H9B	0.61470	0.16630	1.09830	0.1320*
H9C	0.77270	0.23040	1.07430	0.1320*
H10A	0.79540	0.17570	0.44090	0.0500*
H10B	0.87110	0.20060	0.53970	0.0500*
H11A	0.64170	0.42750	0.43460	0.0490*
H11B	0.75450	0.44050	0.51540	0.0490*
H12A	0.78170	0.39070	0.22810	0.0570*
H12B	0.91750	0.24180	0.25140	0.0570*
H13A	1.05010	0.32880	0.06510	0.0700*
H13B	1.03320	0.46390	0.12390	0.0700*
H14A	1.21920	0.44710	0.24480	0.0670*
H14B	1.36030	0.30050	0.26640	0.0670*
H15A	1.11570	0.22360	0.37830	0.0520*
H15B	1.09970	0.36120	0.43340	0.0520*
H16A	0.17160	0.06840	0.71300	0.0840*
H16B	0.38720	0.00790	0.65670	0.0840*
H16C	0.25790	0.07430	0.57490	0.0840*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0372 (2)	0.0676 (2)	0.0380 (2)	−0.0232 (2)	−0.0003 (1)	−0.0024 (1)
O1	0.0540 (6)	0.0738 (7)	0.0406 (5)	−0.0258 (5)	−0.0106 (4)	−0.0033 (4)
O2	0.0495 (6)	0.0739 (7)	0.0429 (5)	−0.0201 (5)	0.0074 (4)	−0.0128 (5)
O3	0.0364 (5)	0.0458 (5)	0.0612 (6)	−0.0141 (4)	−0.0110 (4)	−0.0065 (4)
N1	0.0332 (5)	0.0452 (6)	0.0346 (5)	−0.0165 (4)	−0.0011 (4)	−0.0009 (4)
N2	0.0344 (5)	0.0407 (5)	0.0322 (5)	−0.0144 (4)	−0.0012 (4)	−0.0031 (4)
C1	0.0360 (6)	0.0429 (6)	0.0448 (7)	−0.0163 (5)	−0.0054 (5)	−0.0035 (5)
C2	0.0389 (6)	0.0406 (6)	0.0407 (6)	−0.0150 (5)	−0.0059 (5)	−0.0034 (5)
C3	0.0334 (5)	0.0390 (6)	0.0353 (6)	−0.0152 (5)	−0.0026 (4)	−0.0006 (4)
C4	0.0480 (7)	0.0408 (7)	0.0478 (7)	−0.0115 (6)	−0.0081 (6)	0.0007 (5)
C5	0.0593 (9)	0.0556 (8)	0.0498 (8)	−0.0133 (7)	−0.0140 (7)	0.0106 (6)
C6	0.0453 (7)	0.0845 (11)	0.0437 (7)	−0.0222 (7)	−0.0098 (6)	−0.0002 (7)
C7	0.0564 (8)	0.0637 (9)	0.0458 (7)	−0.0296 (7)	−0.0056 (6)	−0.0099 (6)
C8	0.0460 (7)	0.0430 (7)	0.0447 (7)	−0.0210 (5)	−0.0064 (5)	−0.0018 (5)
C9	0.0772 (13)	0.1301 (19)	0.0518 (10)	−0.0263 (12)	−0.0219 (9)	−0.0022 (10)
C10	0.0330 (6)	0.0421 (6)	0.0391 (6)	−0.0125 (5)	0.0022 (5)	−0.0012 (5)
C11	0.0355 (6)	0.0396 (6)	0.0387 (6)	−0.0126 (5)	0.0018 (5)	−0.0038 (5)
C12	0.0457 (7)	0.0579 (8)	0.0387 (6)	−0.0195 (6)	−0.0102 (5)	−0.0038 (5)
C13	0.0639 (9)	0.0734 (10)	0.0334 (7)	−0.0260 (8)	−0.0045 (6)	−0.0019 (6)
C14	0.0409 (7)	0.0703 (9)	0.0520 (8)	−0.0259 (7)	0.0014 (6)	−0.0080 (7)
C15	0.0355 (6)	0.0517 (7)	0.0395 (6)	−0.0150 (5)	−0.0048 (5)	−0.0055 (5)
C16	0.0533 (8)	0.0466 (8)	0.0683 (9)	−0.0239 (6)	−0.0077 (7)	−0.0058 (6)

Geometric parameters (Å, º) top

S1—C1	1.8295 (14)	C4—H4B	0.9700
S1—C3	1.8410 (14)	C5—H5A	0.9700
O1—C2	1.2197 (16)	C5—H5B	0.9700
O2—C13	1.412 (2)	C6—H6	0.9800
O2—C14	1.4204 (19)	C7—H7A	0.9700
O3—C1	1.3990 (17)	C7—H7B	0.9700
O3—H3	0.8200	C8—H8A	0.9700
N1—C3	1.4688 (15)	C8—H8B	0.9700
N1—C10	1.4659 (18)	C9—H9A	0.9600
N1—C2	1.3420 (19)	C9—H9B	0.9600
N2—C12	1.4633 (17)	C9—H9C	0.9600
N2—C15	1.4651 (19)	C10—H10A	0.9700
N2—C11	1.4636 (17)	C10—H10B	0.9700
C1—C2	1.535 (2)	C11—H11A	0.9700
C1—C16	1.520 (2)	C11—H11B	0.9700
C3—C8	1.524 (2)	C12—H12A	0.9700
C3—C4	1.5298 (19)	C12—H12B	0.9700
C4—C5	1.521 (2)	C13—H13A	0.9700
C5—C6	1.516 (2)	C13—H13B	0.9700
C6—C9	1.521 (2)	C14—H14A	0.9700
C6—C7	1.523 (2)	C14—H14B	0.9700
C7—C8	1.527 (2)	C15—H15A	0.9700
C10—C11	1.5297 (18)	C15—H15B	0.9700
C12—C13	1.513 (2)	C16—H16A	0.9600
C14—C15	1.506 (2)	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600

S1···N1	2.6146 (11)	H5B···H9A	2.4800
S1···H5A	2.8900	H6···H8B	2.5600
S1···H7B	2.8200	H6···H16A^v	2.5100
O1···O3	2.8913 (15)	H7A···H9C	2.5400
O1···C11	3.187 (2)	H7A···H14A^vi	2.5400
O1···C14ⁱ	3.221 (2)	H7B···S1	2.8200
O1···C15ⁱ	3.230 (2)	H7B···O2^x	2.8100
O2···N2	2.8364 (16)	H7B···H5A	2.5600
O3···C15ⁱⁱ	3.3942 (17)	H7B···H9B	2.5300
O3···O1	2.8913 (15)	H8A···H12Aⁱⁱ	2.5600
O3···N2ⁱⁱ	2.8104 (14)	H8B···O3^v	2.7800
O1···H10A	2.5400	H8B···C10	2.7500
O1···H11A	2.6600	H8B···C11	3.0700
O1···H15Bⁱ	2.7500	H8B···H6	2.5600
O1···H16C	2.8000	H8B···H10B	2.3800
O1···H14Bⁱ	2.5200	H8B···H11B	2.4700
O1···H16Bⁱⁱⁱ	2.8200	H8B···H14A^vi	2.4400
O2···H9B^iv	2.7900	H9A···H5B	2.4800
O2···H7B^iv	2.8100	H9B···O2^x	2.7900
O3···H15Bⁱ	2.6400	H9B···C14^x	3.0700
O3···H8Bⁱ	2.7800	H9B···H5A	2.5000
O3···H14Aⁱⁱ	2.9100	H9B···H7B	2.5300
N1···S1	2.6146 (11)	H9B···H14B^x	2.4800
N2···O2	2.8364 (16)	H9C···C12^xi	3.0000
N2···O3ⁱⁱ	2.8104 (14)	H9C···H7A	2.5400
N2···H3ⁱⁱ	2.0000	H10A···O1	2.5400
C2···C11ⁱⁱ	3.5847 (18)	H10A···C12	2.8100
C8···C11	3.4925 (18)	H10A···H12B	2.2700
C11···C8	3.4925 (18)	H10B···C4	2.8100
C11···C2ⁱⁱ	3.5847 (18)	H10B···C8	2.9100
C11···O1	3.187 (2)	H10B···C15	2.7700
C14···O1^v	3.221 (2)	H10B···H4B	2.2500
C15···O1^v	3.230 (2)	H10B···H8B	2.3800
C15···O3ⁱⁱ	3.3942 (17)	H10B···H15A	2.3300
C2···H11A	2.8300	H11A···O1	2.6600
C4···H10B	2.8100	H11A···C2	2.8300
C8···H14A^vi	2.8600	H11A···H12A	2.3700
C8···H10B	2.9100	H11A···C11ⁱⁱ	3.0600
C8···H11B	2.9700	H11A···H11Aⁱⁱ	2.4000
C10···H12B	2.8600	H11B···C8	2.9700
C10···H4B	2.8300	H11B···H8B	2.4700
C10···H15A	2.6800	H11B···H15B	2.5000
C10···H8B	2.7500	H12A···H11A	2.3700
C11···H8B	3.0700	H12A···H8Aⁱⁱ	2.5600
C11···H3ⁱⁱ	2.7100	H12B···C10	2.8600
C11···H11Aⁱⁱ	3.0600	H12B···H10A	2.2700
C12···H3ⁱⁱ	2.9300	H12B···H15A	2.4700
C12···H10A	2.8100	H13B···H14A	2.3400
C12···H9C^vii	3.0000	H14A···H13B	2.3400
C14···H9B^iv	3.0700	H14A···O3ⁱⁱ	2.9100
C14···H3ⁱⁱ	3.0800	H14A···C8^vi	2.8600
C15···H10B	2.7700	H14A···H3ⁱⁱ	2.5900
C15···H3ⁱⁱ	2.7400	H14A···H7A^vi	2.5400
H3···N2ⁱⁱ	2.0000	H14A···H8B^vi	2.4400
H3···C11ⁱⁱ	2.7100	H14B···O1^v	2.5200
H3···C12ⁱⁱ	2.9300	H14B···H9B^iv	2.4800
H3···C14ⁱⁱ	3.0800	H15A···C10	2.6800
H3···C15ⁱⁱ	2.7400	H15A···H10B	2.3300
H3···H14Aⁱⁱ	2.5900	H15A···H12B	2.4700
H4A···H15A^viii	2.5800	H15A···H4A^viii	2.5800
H4B···C10	2.8300	H15B···O1^v	2.7500
H4B···H10B	2.2500	H15B···O3^v	2.6400
H5A···S1	2.8900	H15B···H11B	2.5000
H5A···H7B	2.5600	H16A···H6ⁱ	2.5100
H5A···H9B	2.5000	H16B···O1ⁱⁱⁱ	2.8200
H5A···H5A^ix	2.3300	H16C···O1	2.8000

C1—S1—C3	94.96 (6)	C6—C7—H7B	109.00
C13—O2—C14	109.74 (12)	C8—C7—H7A	109.00
C1—O3—H3	109.00	C8—C7—H7B	109.00
C2—N1—C10	118.36 (10)	H7A—C7—H7B	108.00
C3—N1—C10	121.36 (11)	C3—C8—H8A	109.00
C2—N1—C3	120.12 (11)	C3—C8—H8B	109.00
C11—N2—C15	113.24 (10)	C7—C8—H8A	109.00
C12—N2—C15	109.83 (11)	C7—C8—H8B	109.00
C11—N2—C12	113.29 (11)	H8A—C8—H8B	108.00
S1—C1—C2	104.53 (10)	C6—C9—H9A	109.00
S1—C1—C16	113.45 (10)	C6—C9—H9B	109.00
S1—C1—O3	110.65 (9)	C6—C9—H9C	109.00
O3—C1—C16	107.00 (12)	H9A—C9—H9B	110.00
C2—C1—C16	108.91 (11)	H9A—C9—H9C	109.00
O3—C1—C2	112.40 (11)	H9B—C9—H9C	109.00
O1—C2—C1	121.93 (14)	N1—C10—H10A	109.00
N1—C2—C1	113.93 (11)	N1—C10—H10B	109.00
O1—C2—N1	124.12 (13)	C11—C10—H10A	109.00
S1—C3—N1	103.79 (9)	C11—C10—H10B	109.00
S1—C3—C8	109.34 (9)	H10A—C10—H10B	108.00
N1—C3—C4	111.50 (10)	N2—C11—H11A	108.00
S1—C3—C4	110.49 (9)	N2—C11—H11B	108.00
C4—C3—C8	110.34 (12)	C10—C11—H11A	108.00
N1—C3—C8	111.20 (10)	C10—C11—H11B	108.00
C3—C4—C5	111.95 (11)	H11A—C11—H11B	107.00
C4—C5—C6	112.88 (13)	N2—C12—H12A	110.00
C5—C6—C7	109.51 (14)	N2—C12—H12B	110.00
C7—C6—C9	111.87 (16)	C13—C12—H12A	110.00
C5—C6—C9	110.62 (16)	C13—C12—H12B	110.00
C6—C7—C8	111.54 (12)	H12A—C12—H12B	108.00
C3—C8—C7	111.69 (12)	O2—C13—H13A	109.00
N1—C10—C11	111.71 (11)	O2—C13—H13B	109.00
N2—C11—C10	115.84 (11)	C12—C13—H13A	109.00
N2—C12—C13	109.15 (13)	C12—C13—H13B	109.00
O2—C13—C12	111.53 (12)	H13A—C13—H13B	108.00
O2—C14—C15	111.11 (14)	O2—C14—H14A	109.00
N2—C15—C14	109.61 (11)	O2—C14—H14B	109.00
C3—C4—H4A	109.00	C15—C14—H14A	109.00
C3—C4—H4B	109.00	C15—C14—H14B	109.00
C5—C4—H4A	109.00	H14A—C14—H14B	108.00
C5—C4—H4B	109.00	N2—C15—H15A	110.00
H4A—C4—H4B	108.00	N2—C15—H15B	110.00
C4—C5—H5A	109.00	C14—C15—H15A	110.00
C4—C5—H5B	109.00	C14—C15—H15B	110.00
C6—C5—H5A	109.00	H15A—C15—H15B	108.00
C6—C5—H5B	109.00	C1—C16—H16A	109.00
H5A—C5—H5B	108.00	C1—C16—H16B	109.00
C5—C6—H6	108.00	C1—C16—H16C	109.00
C7—C6—H6	108.00	H16A—C16—H16B	109.00
C9—C6—H6	108.00	H16A—C16—H16C	109.00
C6—C7—H7A	109.00	H16B—C16—H16C	109.00

C3—S1—C1—O3	−136.07 (10)	C12—N2—C15—C14	56.88 (15)
C3—S1—C1—C2	−14.85 (9)	C12—N2—C11—C10	71.48 (15)
C3—S1—C1—C16	103.66 (11)	S1—C1—C2—N1	12.26 (13)
C1—S1—C3—N1	13.84 (9)	O3—C1—C2—O1	−49.39 (17)
C1—S1—C3—C4	−105.81 (9)	O3—C1—C2—N1	132.32 (12)
C1—S1—C3—C8	132.57 (9)	C16—C1—C2—O1	69.00 (17)
C14—O2—C13—C12	−59.69 (17)	C16—C1—C2—N1	−109.30 (13)
C13—O2—C14—C15	59.60 (16)	S1—C1—C2—O1	−169.45 (11)
C2—N1—C10—C11	79.30 (14)	N1—C3—C8—C7	−178.85 (12)
C3—N1—C2—O1	179.78 (12)	C8—C3—C4—C5	52.97 (16)
C10—N1—C2—O1	−4.83 (19)	S1—C3—C8—C7	67.13 (14)
C3—N1—C10—C11	−105.38 (13)	N1—C3—C4—C5	177.06 (13)
C2—N1—C3—C8	−126.75 (13)	C4—C3—C8—C7	−54.59 (16)
C10—N1—C3—C8	58.01 (15)	S1—C3—C4—C5	−68.06 (15)
C10—N1—C2—C1	173.42 (10)	C3—C4—C5—C6	−54.55 (19)
C2—N1—C3—C4	109.65 (14)	C4—C5—C6—C7	55.23 (18)
C2—N1—C3—S1	−9.30 (13)	C4—C5—C6—C9	178.97 (16)
C10—N1—C3—S1	175.45 (9)	C5—C6—C7—C8	−56.25 (18)
C10—N1—C3—C4	−65.59 (15)	C9—C6—C7—C8	−179.25 (16)
C3—N1—C2—C1	−1.97 (16)	C6—C7—C8—C3	57.30 (18)
C11—N2—C12—C13	175.83 (12)	N1—C10—C11—N2	−169.01 (11)
C15—N2—C11—C10	−54.44 (15)	N2—C12—C13—O2	58.47 (17)
C15—N2—C12—C13	−56.45 (15)	O2—C14—C15—N2	−58.52 (16)
C11—N2—C15—C14	−175.38 (11)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x+1, y, z−1; (v) x+1, y, z; (vi) −x+2, −y+1, −z+1; (vii) x, y, z−1; (viii) −x+2, −y, −z+1; (ix) −x+1, −y, −z+2; (x) x−1, y, z+1; (xi) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2ⁱⁱ	0.82	2.00	2.8104 (14)	169
C7—H7B···S1	0.97	2.82	3.2235 (18)	106
C14—H14B···O1^v	0.97	2.52	3.221 (2)	129

Symmetry codes: (ii) −x+1, −y+1, −z+1; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₈N₂O₃S
M_r	328.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.0753 (4), 10.2002 (5), 11.8734 (6)
α, β, γ (°)	82.467 (4), 71.487 (4), 68.965 (4)
V (Å³)	865.44 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.73 × 0.45 × 0.29

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.867, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	18220, 3693, 3319
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.637

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.093, 1.04
No. of reflections	3693
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.21

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2ⁱ	0.82	2.00	2.8104 (14)	169
C7—H7B···S1	0.97	2.82	3.2235 (18)	106
C14—H14B···O1ⁱⁱ	0.97	2.52	3.221 (2)	129

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z.

Acknowledgements

The authors thank the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for use of the Stoe IPDS II diffractometer (purchased under grant No. F.279 of the University Research Fund). This work was supported by the Research Fund of İstanbul University (project Nos. 177/15012004 and UDP-730/05052006).

References

Akkurt, M., Yalçın, Ş. P., Gürsoy, E., Güzeldemirci, N. U. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3103. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 64| Part 8| August 2008| Pages o1574-o1575

doi:10.1107/S1600536808022447

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

rac-2-Hy­droxy-2,8-di­methyl-4-morpho­lino­ethyl-1-thia-4-aza­spiro­[4.5]decan-3-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-2-Hydroxy-2,8-dimethyl-4-morpholinoethyl-1-thia-4-azaspiro[4.5]decan-3-one